(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-benzylamide → (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-2-hydroxymethyl-propoxy)-3,5-dimethyl-benzylamide

HRID 2353616Notes

Reaction equation

HRID 2353616 reaction equation
CC1(C)[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:31]([CH3:32])=[CH:30][C:13]([CH2:14][NH:15][C:16]([C:18]3[S:25][C:24]([CH3:26])=[C:23]4[C:19]=3[CH2:20][C@H:21]3[C:27]([CH3:29])([CH3:28])[C@H:22]34)=[O:17])=[CH:12][C:11]=2[CH3:33])[CH2:4][O:3]1>C(O)(=O)C.O>[OH:7][CH2:6][CH:5]([CH2:4][OH:3])[CH2:8][O:9][C:10]1[C:11]([CH3:33])=[CH:12][C:13]([CH2:14][NH:15][C:16]([C:18]2[S:25][C:24]([CH3:26])=[C:23]3[C:19]=2[CH2:20][C@H:21]2[C:27]([CH3:29])([CH3:28])[C@H:22]23)=[O:17])=[CH:30][C:31]=1[CH3:32]

Participants

4

Reactant 1

HCID 68451511(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-benzylamide

Product 1

HCID 11554056(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-2-hydroxymethyl-propoxy)-3,5-dimethyl-benzylamideYield 85.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-benzylamide (28 mg, 0.058 mmol) in acetic acid (1.6 mL) and water (0.4 mL) is stirred at rt for 1 h before it is separated by prep. HPLC to give (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-2-hydroxymethyl-propoxy)-3,5-dimethyl-benzylamide (22 mg) as a colourless solid. LC-MS: tR=0.96 min, [M+1]+=444.30; 1H NMR (CDCl3): δ 6.95 (s, 2H), 5.77 (t br, J=5.8 Hz, 1H), 4.51-4.37 (m, 2H), 4.00 (d, J=5.3 Hz, 4H), 3.90 (d, J=5.3 Hz, 2H), 2.93 (dd, J=5.9, 17.6 Hz, 1H) 2.73 (d, J=17.6 Hz, 1H), 2.36 (s, 3H), 2.33-2.20 (m, 9H), 1.93-1.86 (m, 2H), 1.12 (s, 3H), 0.74 (s, 3H).

Workup

  1. customis separated by prep

Sources & evidence

ORD record
ord-bcb9e295a4394a0a9add7433202e0a0e
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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